Phenyl isocyanate → 1-(m-nitrophenyl)-3-methylquinazoline-2,4(1H, 3H)-dione
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[NH:7][C:8]1[CH:17]=[CH:16]C=CC=1C(NC)=O)([O-:3])=[O:2].[NH2-].[Na+].[C:23]1([N:29]=[C:30]=[O:31])C=CC=CC=1.[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:35](=[CH:34][CH:33]=[CH:16][CH:17]=3)[C:36](=[O:32])[N:29]([CH3:23])[C:30]2=[O:31])[CH:18]=[CH:19][CH:20]=1)([O-:3])=[O:2]Participants
5
Procedure
To a solution of 2.6 g of 2-(m-nitroanilino)-N-methylbenzamide and 20 ml of tetrahydrofuran was added 0.86 g of sodium amide, and the whole was stirred for 30 minutes at room temperature. To this was added dropwise under cooling 3.6 g of phenyl isocyanate, and the mixture was stirred for one hour at room temperature, and then refluxed for 4 hours. After the reaction was finished, the solvent was distilled off from the resulting mixture. The residue thus obtained was recrystallized from methanol to give 2.2 g of 1-(m-nitrophenyl)-3-methylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 241°-242° C.
Workup
- additionTo this was added dropwise
- stirringthe mixture was stirred for one hour at room temperature
- temperaturerefluxed for 4 hours
- distillationthe solvent was distilled off from the resulting mixture
- customThe residue thus obtained
- customwas recrystallized from methanol
Sources & evidence
- ORD record
- ord-3d190200007843629bd8c455f1e6cc17
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04016166
Reaction notes
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